Formation and characterisation of alkoxy derivatives of [60]fullerene

被引:44
作者
Avent, AG [1 ]
Birkett, PR [1 ]
Darwish, AD [1 ]
Houlton, S [1 ]
Taylor, R [1 ]
Thomson, KST [1 ]
Wei, XW [1 ]
机构
[1] Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2001年 / 05期
关键词
D O I
10.1039/b009673n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heating C60Cl6 with either methanol or propan-2-ol under reflux during 140 h yields 1,4-(MeO)(2)C-60 and 1,4-(iPrO)(2)C-60, respectively, the latter reaction being faster due to the greater nucleophilicity of propan-2-ol. The reaction between C60Cl6 and ROH-NaOR yields C-60(OR)(5)Cl (R=Me, Et) both of which are isostructural with C60Ar5Cl. A by-product of the reaction with ethanol-sodium ethoxide is 1,4-(EtO)(2)C-60 showing that chlorine elimination accompanies substitution; this parallels the formation of 1,4-Ph2C60 from the reaction between C60Cl6 and benzene-FeCl3.
引用
收藏
页码:782 / 786
页数:5
相关论文
共 17 条
[1]   A hexaallyl[C60]fullerene, C60(CH2CH=CH2)6 [J].
Abdul-Sada, AK ;
Avent, AG ;
Birkett, PR ;
Kroto, HW ;
Taylor, R ;
Walton, DRM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (03) :393-395
[2]   Isolation and characterisation of Cs-symmetry C60Me5O2OH, the first methylated fullerenol;: a bis-epoxide with two oxygens in a pentagonal ring [J].
Al-Matar, H ;
Hitchcock, PB ;
Avent, AG ;
Taylor, R .
CHEMICAL COMMUNICATIONS, 2000, (12) :1071-1072
[3]   Spontaneous oxidation of C60Ph5X (X=H, Cl) to a benzo[b]furanyl[60]fullerene [J].
Avent, AG ;
Birkett, PR ;
Darwish, AD ;
Kroto, HW ;
Taylor, R ;
Walton, DRM .
CHEMICAL COMMUNICATIONS, 1997, (16) :1579-1580
[4]  
AVENT AG, UNPUB
[5]   PREPARATION AND C-13 NMR SPECTROSCOPIC CHARACTERIZATION OF C-60CL6 [J].
BIRKETT, PR ;
AVENT, AG ;
DARWISH, AD ;
KROTO, HW ;
TAYLOR, R ;
WALTON, DRM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (15) :1230-1232
[6]   Preparation and characterisation of unsymmetrical C(60)Ph(4) and symmetrical C(60)Ph(2): The effect of regioselective nucleophilic attack upon C60Cl6 [J].
Birkett, PR ;
Avent, AG ;
Darwish, AD ;
Kroto, HW ;
Taylor, R ;
Walton, DRM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (03) :457-461
[7]   C60F18O, the first characterised intramolecular fullerene ether [J].
Boltalina, OV ;
de La Vaissière, B ;
Fowler, PW ;
Hitchcock, PB ;
Sandall, JPB ;
Troshin, PA ;
Taylor, R .
CHEMICAL COMMUNICATIONS, 2000, (14) :1325-1326
[8]   Photolysis of dialkoxy disulfides: A convenient source of alkoxy radicals for addition to the sphere of fullerene C-60 [J].
Borghi, R ;
Lunazzi, L ;
Placucci, G ;
Cerioni, G ;
Plumitallo, A .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3327-3331
[9]   ADDITION OF ALKYLTHIO AND ALKOXY RADICALS TO C-60 STUDIED BY ESR [J].
CREMONINI, MA ;
LUNAZZI, L ;
PLACUCCI, G ;
KRUSIC, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4735-4738
[10]   Novel base-catalysed formation of benzo[b]furano[60]- and -[70]fullerenes [J].
Darwish, AD ;
Avent, AG ;
Kroto, HW ;
Taylor, R ;
Walton, DRM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (10) :1983-1988